Methanol → 2-(4-Methylphenyl)ethanimidamide hydrochloride

Participants

Reaction Conditions

Reaction Steps

10.8 g (201 mmol) of ammonium chloride are suspended under argon in 200 ml of dry toluene and the suspension is cooled to 0° C. 100 ml of a 2M solution of trimethylaluminium in hexane are added dropwise and the mixture is stirred at room temperature until the evolution of gas is complete. After addition of 13.2 g (100 mmol) of 4-methylbenzyl cyanide, the reaction mixture is stirred overnight at 80° C. (bath). The cooled reaction mixture is treated with 35 ml of methanol and then stirred at room temperature for a further 1 h. The solid is then first filtered off with suction, and the filter cake is washed several times with methanol. The filtrate is concentrated, resuspended in dichloromethane/methanol 10/1, and the insoluble solid is filtered off. The solvent is then again evacuated from the filtrate in vacuo.

Provenance & Evidence